It’s hard to feel a deep sense of pity for someone who has had the privilege of stepping down at the age of 55 after earning over $40 million coaching college basketball, simply because he no longer finds it rewarding.

Moreover, constantly lamenting the golden days of college basketball when scholarships and future prospects were enough to entice players to join a legendary coach serves no purpose – and this trend may become more frequent moving forward.

Tony Bennett has exited college basketball, and all parties involved will move on. Bennett will discover new paths for fulfillment, the Virginia program will transition into a new phase, and the NCAA tournament will proceed to generate incredible revenue. By the next spring, Bennett’s presence will likely only be felt in sports commentary, a role that closely resembles his status since Virginia captured the national title over five years ago.

While it may seem brazen and somewhat inappropriate to end such a prominent career just weeks before the season kicks off, it shouldn’t come as a shock. Bennett is not suited for this evolving environment where monetary incentives heavily influence recruiting, and college athletes frequently switch programs to suit their needs. As Virginia’s consistent success started to fade amid the NIL landscape, the hushed concerns from Bennett’s peers grew louder, signaling it would not be long before he stepped back.

“Upon self-reflection, I realized I am no longer the best coach to guide this program in today’s climate,” Bennett shared during an emotional press conference on Friday, making it clear what drove his decision. “There is still a way to uphold our values in this context, but it is complex. Admitting that I’m not prepared for this challenge is humbling. While player revenue is justified, the state of college athletics feels unhealthy.”

Although the sport’s appeal will persist, with March Madness retaining its strong allure, Bennett’s concerns echo those of many others regarding the future of college basketball.

It’s inadequate to label these sentiments as simply complaints from disgruntled middle-aged men who have profited immensely while witnessing athletes finally reclaim their agency.

In recent times, I’ve seen basketball coaches with whom I’ve had long-standing relationships—usually supporters of player rights—grow increasingly disillusioned with the transactional essence that now permeates college basketball.

It’s not fundamentally about cutthroat recruiting battles, as it has always been a ruthless landscape. Every coach had to determine their limits to procure talent. In some respects, making the deals transparent has produced a form of liberation.

What has drastically changed is the nature of relationships. Coaches at lower levels recognize that any promising recruit will likely depart the moment a better opportunity arises. At higher levels, the constant possibility of losing a player looms large over nearly every conversation.

No one is disputing that players should earn money. The concern lies in how the current chaotic, free-market framework has rendered meaningful connections between coaches and players impossible.

It may be out of style to assert, but young athletes aged 18 to 22 still require guidance, development, and structure to reach their full potential both as individuals and collectively. A program like Virginia, once managed effectively by Bennett, inevitably struggled against these current circumstances.

De’Andre Hunter, who was the standout on Virginia’s 2019 championship team, redshirted his initial year since he would not have received significant playing time. He later emerged as the fourth pick in the NBA draft. Malcolm Brogdon was honed over five years and has earned over $110 million professionally. Joe Harris committed to Bennett’s philosophy before Virginia achieved any accolades and secured an ACC title in his final year.

All coaches, particularly in basketball, acknowledge that such scenarios are unlikely to recur. They will be disrupted by the demands for playing time and outrageous financial expectations, along with a wave of NIL representatives who lack the experience to negotiate even the simplest agreements.

“Nick Nurse and I share a good rapport,” noted Steve Forbes from Wake Forest, referencing the coach of the Philadelphia 76ers. “He often asks, ‘How do you navigate this?’ For me, the toughest part isn’t recruiting; it’s retaining talent. I understand my players’ aspirations, but I’m like, ‘Are you out of your mind?’ This is precisely why professional teams have general managers—they handle player relations.”

Ironically, it’s startling how many coaches still wish to remain in this profession under current circumstances. An increasing number of coaches in their 40s are expressing feelings of year-round stress, displaying cynicism toward player expectations, and are actively considering leaving once they attain a comfortable financial position.

These opinions are often easy to ridicule, especially coming from sales professionals who have profited greatly from the efforts of young individuals, often prioritizing financial gain over loyalty in their career choices.

However, they’re now realizing what many of us have been arguing for years: For the NCAA to adhere to antitrust regulations and maintain some sense of order, they need to negotiate a new approach that includes salary caps, contracts, and limitations on how players can move between teams.

It’s quite surprising—and frankly, disrespectful—that university presidents are still unwilling to explore this path, instead pinning their hopes on NCAA president Charlie Baker, a former governor of Massachusetts, to persuade lawmakers to introduce accommodating legislation.

A few years back, almost every coach and athletic director would have supported that initiative. Now, dissent is starting to appear.

Just recently, I spoke with a well-respected athletic director from a notable institution who criticized Baker for not implementing any substantial changes compared to his predecessor, Mark Emmert, despite taking office with a reputation for being a bipartisan reformer who managed a liberal state as a conservative.

Moreover, during the recent ACC basketball media days, coaches expressed a desire for a system that would allow players to sign contracts similar to those in professional sports.

“People argue that ‘well, coaches can leave,’ ” Forbes mentioned. “But we really can’t. Sure, we can leave, but there’s a buyout. These players can transfer without any penalties. It’s challenging to uphold that structure. I would feel much more comfortable with a more professional business model when it comes to our players.”

This issue extends beyond the sleeping habits of college basketball coaches. If Bennett or anyone like him is no longer interested in their role, there are countless others prepared to tackle those challenges, along with the lucrative pay.

Yet, it feels like we’re approaching a pivotal moment for the entire American developmental system.

Due to the NCAA’s misguided legal strategies and stubbornness, they’ve quickly shifted from a position of control to one of chaos, with virtually no rules in place. Consequently, many student-athletes enter college aiming to extract as much as possible from every opportunity, often disregarding other essential elements—like the guidance of skilled coaches—that greatly influence their future prospects.

To assume that this trend won’t negatively affect how certain players transition to the NBA or NFL would be incredibly simplistic. In fact, teams in both leagues are already noticing these issues and having to take them into consideration.

While these may not rank among the world’s most pressing problems, it would be unwise to overlook them. Bennett’s decision to retire is merely another example of a system that is failing and urgently requires attention. People may not care if a wealthy coach is unhappy in their role, but what about the implications of a healthy 55-year-old coaching legend stepping away from their lifelong commitment?

If the NCAA fails to face the facts— and quickly—a growing number of individuals may choose to follow Bennett’s lead and exit as well.